Aldol

Condensation
BY
MEHWISH KHUSBASH
 Aldol Condensation

ALDOL CONDENSATION is possible

only when the carbonyl compound
contains atleast one α-hydrogen atom.
 Aldol Condensation

Thus the following Aldehydes or ketones having no

α-hydrogen atom do not undergo Aldol
Condensation.
 Some conditions regarding
the Aldol Reaction
 A reversible equilibrium
 OH is the base typically used in an aldol reaction.
 Aldol reactions can be carried out with either aldehydes or
 ketones.
 With aldehydes, the equilibrium favors products
 With ketones the equilibrium favors the starting materials.
Aldol
Condensation
 Aldol
Condensation
Step 1:
First, an acid-base reaction. Hydroxide functions as a base and
removes the acidic a-hydrogen giving the reactive enolate .
Step 2:
The nucleophilic enolate attacks the aldehyde at the
electrophilic carbonyl C in a nucleophilic addition type
process giving an intermediate alkoxide.
Step 3:
An acid-base reaction. The alkoxide deprotonates a water
molecule creating hydroxide and the β-hydroxyaldehydes or
aldol product.
 Step:1

An enolate ion is the anion formed when an alpha

hydrogen in the molecule of an aldehyde or a ketone is
removed as a hydrogen ion.
 Step:2

The alkoxide ion is the conjugate base of

alcohols.
Aldol Condensation
 Aldol Condensation
 The aldol condensation is facilitated by-I groups on the
carbonyl component and retarted by +I groups as
described in CHзCHO and CHзCOCHз condensations.
 The condensation is readily reversible and the position
of equilibrium is not always favorable to the product.
 Eg:
 Aldol Condensation
LIMITATIONS:
Aldol products,as such, are not always isolated
from the reaction mixture.eg:acetaldol readily forms a
cyclic hemi-acetol.
EXTENSIONS:
Aldol condensation can occur between
 Two identical or different aldehydes
 Two identical or different ketones
 An aldehyde and a ketone
 Aldol Condensation
 The R groups may be H, alkyl, or aryl. When the R groups in one
molecule are different than those in the other, the reaction is called a
crossed-aldol reaction. The ability to join different aldehydes and ketones
together is what give this process its synthetic value.
 The name aldol condensation is also commonly used, especially in
biochemistry, to refer to just the first stage of the process the aldol
reaction itself as catalysed by
aldolases.
 Aldol Condensation

In its usual form ,it involves the nucleophilic

addition of a ketone enolate to an aldehyde to
form a β-hydroxy ketone or
aldol(aldehyde+alchohol), a structural unit
found in many naturally occurring molecules
and pharmaceuticals.
Aldol Condensation

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